N-halogenated amino acid formulations

Abstract

The present invention relates to a method for treating a tissue infection comprising contacting the infected tissue with a pharmaceutically effective amount of a formulation comprising a N-halogenated amino acid and a phase transfer agent. This specification also describes a formulation having antimicrobial activity comprising a N-halogenated amino acid and a phase transfer agent.

Description

CROSS-REFERENCE TO RELATED APPLICATION[0001]This application claims priority under 35 U.S.C. §119 to U.S. Provisional Patent Application No. 60 / 915,291 filed May 1, 2007, the entire contents of which are incorporated herein by reference.TECHNICAL FIELD OF THE INVENTION[0002]The present invention relates to methods for improving the antimicrobial properties of N-halogenated amino acid compounds and formulations. The present invention further relates to N-halogenated amino acid-containing formulations with improved antimicrobial properties.BACKGROUND OF THE INVENTION[0003]It is generally desirable to use the minimum quantity of an antimicrobial compound necessary to achieve desired effects. This is because undesirable side-effects are more probable when higher concentrations of an antimicrobial are used at a delivery site through the use of, for example, high concentration formulations, more frequent dosing, or longer-duration treatment. Unfortunately, while the use of lower concentra...

AI Technical Summary

Benefits of technology

[0009]The present invention further relates to N-halogenated amino acid-containing formulations with improved antimicrobial characteristics. These formulations comprise a N-halogenated amino acid such as, for example, 2,2-dimethyl-N,N-dichlorotaurine and a phase transfer agent such as a quaternary amine. The formulations of the present invention have excellent antimicrobial activity, and allow the use of low concentrations of the N-halogenated amino acid compounds by increasing their efficacy.

[0010]While not desiring to be bound by theory, it is believed that some phase transfer agents, such as quaternary amine compounds, form ion pairs with N-halogenated amino acid compounds. Alone, N-halogenated amino acid compounds are very polar and poorly penetrate lipophilic tissues. Ion pairs formed with such ion pairing agents as quaternary amines are believed to increase the antimicrobial efficacy of the N-halogenated amino acid compounds. Ion pairing may improve the penetration of the N-halogenated amino acid compounds through lipophilic tissues. Other phase transfer agents may improve the apparent permeability of N-halogenated amino acids by mechanisms other than ion pair formation, also resulting in improved antimicrobial properties.

[0011]Previous observations noted that ammonium chloride can enhance the activity of N-chlorotaurine, likely due to the formation of chloroamine compounds resulting from decomposition of the N-chlorotaurine. In these cases, the anti-infective activities are not derived from N-chlorotaurine alone, but from a reaction product or from the contribution of a reaction product's anti-infective activity. In contrast, certain embodiments of the present invention enhance the activity of N-halogenated amino acid compounds by the formation of ion pairs with phase transfer agents, and do not cause degradation of the N-halogenated amino acid and its salts.

[0013]Another embodiment of the present invention is a method for improving the antimicrobial activity of a formulation comprising a N-halogenated amino acid. The method comprises adding a phase transfer agent to the N-halogenated amino acid formulation.

Problems solved by technology

Alone, N-halogenated amino acid compounds are very polar and poorly penetrate lipophilic tissues.

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